A Cascade of Interesting Chemistry

The selective incorporation of functional groups, particularly hydroxy and amino groups, into small molecules is a major challenge facing the synthetic organic chemist. Typically, methods for incorporating such groups require the interconversion of existing functionality which may require many steps rendering these transformations laborious, costly and time consuming.

Simmons and Hartwig have recently described the method for introducing β-hydroxy groups through a formal iridium catalysed C-H activation method directed by proximal silyl ethers. This strategy exploits the affinity of silicon for transition metals, in this case iridium, to direct the formation of a C-Si bond. The resulting oxasilolane was then transformed, by a Tamao-Fleming oxidation, to the corresponding 1,3-diol. For ease of isolation, the diols were finally acetylated to give the 1,3-diacetates.

The versatility of this methodology is demonstrated by converting both simple and complex alcohols into the 1,3-diol analogues.